Bill Simmons Is Trying Something Ambitious, But He’s Not an Underdog


Bill Simmons’s new website, The Ringer, is launching this week, and there will surely be much fanfare. It alternately feels like yesterday and forever ago that Simmons learned he was “leaving” ESPN on Twitter last May. Simmons has spent that time preparing a new weekly show on HBO, which debuts in a few weeks, and also assembling a militia under his own umbrella.

All told, Simmons has about 50 staffers at his site. The stakes of success and failure, however you quantitatively and qualitatively define them, are high for both ventures. With The Ringer, Simmons is betting big that his media group will be able to scale monetization and distribution across a variety of platforms, and he sent out this string of defiant tweets last weekend:

Launched the BS Podcast on Oct. 1 and it will exceed 50 million downloads by the end of next week. Motherships are overrated. The best thing about making content in 2016 – if you have good content, people are going to find it no matter who you are and where you are. We’ve launched 6 other podcasts to great success and we’re going to launch 5 more soon. People will find them. It’s 2016. This isn’t hard.

We’re going to launch @ringer next month – the site is going to be good immediately. People will find it. Quality is always going to win. We didn’t spend 1 dollar promoting our 7 @ringer podcasts – no ads, no favor-trading, nothing. Just Twitter and FB and cross-promotion.

At first blush, this seems quite self-absorbed. Simmons went from being featured on Page 2 alongside Hunter S. Thompson, Ralph Wiley, and David Halberstam, to getting the keys to Grantland, to appearing on their NBA pregame show for two years. Does he not realize that 15 years of exposure at ESPN contributed to his brand recognizance for distributing his podcast, and building the publishing cachet attractive to investors? HBO might not be funding this, but when they’re promoting his show prolifically on Facebook and on 42nd Street billboards, doesn’t that also contribute? Who didn’t believe he could have a successful podcast without ESPN?

Simmons has individual digital reach that is unprecedented in sports media. While he’s correct that the barriers to entry in starting a new publication are low, few–if any others–have the gravitas to eschew standard cost constraints and go full throttle at launch like he has. It’s one thing to gloat about what he’s built, but it’s another to act like this is a replicable blueprint. You’re not going to find the money for 50 staffers and LA-area office space lying on the ground.

As far as we can count, this is their masthead so far (* denotes part-time; many if not most of the writers and editors will also appear regularly on podcasts):

Graphic by Michael Shamburger
Graphic by Michael Shamburger /

To understand where Simmons may have been coming from here, we have to rewind a little bit. Without rehashing every nook and cranny of the ESPN fissure, here goes:

On a recent podcast with Chris Sacca – a Shark Tank judge, veteran of Google, and early investor in Twitter and Uber – Simmons said that he really began immersing himself in entrepreneurialism and venture capital and angel investing after he was suspended for three weeks for calling Roger Goodell a liar (and, more consequentially, daring his bosses to do something about it): “I just kind of went into this abyss of the whole world. How do you start a business? What are people like? What do they invest in? And I became more and more fascinated by all of it.”

Simmons recently told Mike Francesa that as far as Grantland went with ESPN, the clashes weren’t necessarily over content, but that he met resistance when he wanted to expand. “Fundamentally we just didn’t make sense for ESPN because their ad sales model is to get advertisers to spend lots of money, and then they take that money and put it on their biggest properties … Their ad sales people are incentivized to get the money to go in that direction. So then you have us, and we’re trying to operate like a little business within ESPN, and it just never really fit. It was always rocky.”

Simmons continued: “It was never a directive from ESPN to us that we had to make money, but then when you start battling with them and you need more resources that’s when they start pointing to the budget and things like that. I’m super grateful to them for all the chances they gave me…”

This opinion mirrors what he told Peter Kafka last March when he was fighting with ESPN to add more verticals; he thought they could have been doing a better job on selling his podcast, and then to have that money reinvested in Grantland. (If this were Simmons’ only issue at ESPN, it probably could have been resolved, but combined with a rocky stretch on the NBA show, and obviously everything with Goodell, it was best for all sides to move on when they did.)

Part of the money for Ringer’s launch is likely coming from podcast revenue. There’s no way to know how much they’re making, but ESPN oral history author Jim Miller had an industry source who estimated in October that Simmons’ podcast alone was worth $5 million in revenue; they’ve since added more streams, and had dozens of businesses advertise, including SeatGeek, Callaway, and Yahoo Sports as presenting sponsors.

Simmons has gone back and forth between being outwardly bitter and thankful toward ESPN. In the former category, there was the tweet string above, and gripes about softball interviews of Roger Goodell from Chris Berman, as well as a threat to hire an outside ombudsman. And then there are other times when he sounds more in the “all’s well that ends well” camp.

“It’s honestly like we got divorced and there’s the natural bitterness you have afterwards,” he told Francesa. “But now it’s like you look at it and I’m in an awesome place. That place is still making a ton of money. I learned a lot. I got a lot of great opportunities. The bottom line is now I get to work with all people that I love working with. I get to work with HBO, which treats their talent better than anybody. It worked out great for me so it’s really tough for me to be that bitter about it at this point.”

In any event, it feels like launching The Ringer with 40-odd staffers as opposed to dipping toes in the water with, say, 25 and branching out from there has a lot to do with being motivated to prove to ESPN, to say nothing of various others that said he couldn’t do this, that he can. He said on a recent podcast that his team had originally intended to launch with less writers, but that it “snowballed.” (For comparison’s sake, The Big Lead has eight staffers.)

With everyone, there’s the threat of getting lost outside of ESPN. Michelle Beadle always gets brought up as an example here. However, staying relevant is less than half of this battle; Simmons is hellbent on proving he can be profitable on his own at the size and scale he’s commanding. We may never truly know the details on whether revenue exceeds cost; if we ever do, it will require a public sale (or folding). That’s years away, at the earliest.

(Also: One big variable in early profitability for Simmons’ overall firm will be how much he is or isn’t paying himself for his podcast and for running The Ringer. If he’s indeed drawing the $5 million per year Miller’s source estimated, he could reinvest that in 50 employees making $100k annually.)

There are myriad challenges Simmons faces that have nothing to do with his site’s content. For example, what if there’s a broader economic downturn and advertising budgets dry up? Could he escape having to preside over layoffs, which have even affected new media successes like Buzzfeed and Vice?

Almost no numbers mean as little as when an article uncritically cites someone’s Twitter followership. There are so many bots out there, and no reliable way to measure who’s got how many following them. That being said, we can observe someone’s true Twitter reach anecdotally with Chartbeat, which shows us our real-time traffic and where it’s coming from. Here, the couple of times Simmons has shared our posts, every other sports media member’s reach is dwarfed. If you produce quality content, people will see it, if he shares it. However, there can be diminishing returns on his feed if he’s flooding the market, and Twitter is really the only platform that is fully under a publisher’s control.

As Simmons is aware, he’s launching a website at a time when websites are becoming increasingly antiquated, and it sounds like The Ringer will be Everywhere. Instagram and Snapchat don’t send outbound traffic. Can Simmons’s people, or anyone else for that matter, find a viable market there for sponsored content?

Publications are getting half the engagement on Facebook posts that direct users back to their own site as they were a year ago; we’re all “serfs in their kingdom” who can be evicted at any time. Live videos are where the firehose is directed now. How long will it stay that way?

A jillion young people are on Snapchat all day, but the platform has all the leverage over the institutional publishers on its ‘Discover’ page, provided you can even get yourself there. Snapchat and Facebook will be just fine for themselves going forward, but it’s an understatement to say it’s a challenge to figure out how to make more money than you spend on and with them.

From a content perspective, you probably have a decent idea of what to expect in the Ringer’s sports and culture coverage. While single-sport cornerstones like Zach Lowe and Bill Barnwell are still at ESPN and Jonah Keri has a thousand other gigs, there are enough Grantland ex-pats at The Ringer that the writing should be relatively familiar.

There are a couple of differences, though. For one, Simmons told Francesa that his new staff is younger and will be “more reactionary” than Grantland’s, and that there will also be a tech vertical. This is where there’s real intrigue, and it also begs the question: Who is helping to fund the Bill Simmons Media Group (BSMG) and by extension the launch of this site?

When we posed the funding question to SI’s Richard Deitsch, he had a theory but no concrete answer. “I honestly don’t know but if I had to guess I’d think there’s some venture capitalists or Silicon Valley or Hollywood types who have invested.”

Good luck to anyone in figuring that out. Simmons and his inner circle are strictly unified when it comes to omerta and preventing leaks they don’t want Out There. We’re frankly not going to learn who is funding BSMG unless or until they want us to know (a rep for Simmons declined to comment on this). However, for as long as this remains the case, it raises some questions about tech coverage, which has greater real-life stakes than Kevin Durant’s placement on the pyramid or “Is Ryan Reynolds a Star?”.

On the podcast with Chris Sacca, it was mentioned that he and Simmons had been to multiple “jam sessions” together, which the two described as free-form discussions amongst sharp minds in Silicon Valley about where sometimes-specified things are headed in the future. To be clear, there was not any indication that Sacca was an investor in Simmons, but there did exist a mutual familiarity and friendship. As we mentioned before, Simmons has been embedding himself in the Silicon Valley community since September of 2014.

Now, of course Simmons is going to be friends with titans of industry, because he’s one himself. It gets a little bit murkier if The Ringer is covering, say, Andreessen Horowitz. This venture capital firm is a behemoth, and invested in dozens of companies including Air BNB, Buzzfeed, and Facebook. Last September, they led a $57 million financing round in Medium, the publishing platform run by former Twitter CEO Evan Williams, which will host The Ringer’s content. They upped their stake in April. Other investors in Medium include Google Ventures and Spark Capital, another big VC shop. Simmons said on a recent podcast that Ringer has editorial autonomy on Medium, which must’ve been a prerequisite after everything that happened with his Goodell commentary.

If there are Goodell-like leaders in Silicon Valley, how hard will Simmons and/or the Ringer go after them? Bay Area technocrats are notoriously thin-skinned about aggressive coverage, and much of the access press abides. The New York Times wrote this past week:

Twenty-five years ago, tech coverage was the domain of geeks and trade reporters — people who understood their way around a motherboard, were excited by it and wouldn’t dream of crossing certain boundaries. Now, with tech at its zenith, much of the coverage of the industry is still done by enthusiasts. Combine this with the need to get the power players to come to the media’s conferences and there is a real reluctance to look behind the scenes.

Seemingly everything in Silicon Valley is interconnected, and there is the potential for conflict of interest in everything they cover. When relationships are transparent, this is the way of the world now. For example, when Ringer’s culture vertical covers HBO, everyone will know that Simmons also works there; our website’s media coverage will be under a microscope when our editor-in-chief Jason McIntyre becomes an on-air personality at FS1 in June.

In the past, Simmons has astutely observed that “everyone [in the media] has alliances” and sources they protect, and was hesitant to define himself as a journalist at a time where nobody really knows what that even means anymore. Grantland had some reporting, but as Ty Duffy wrote, much of its content was longform blogging. The Ringer will seek to be informative and entertaining, but we won’t know for awhile how aggressively they intend to hold powerful figures and institutions in tech to task. Whether they do or don’t is their own prerogative.

However, the dynamics feel different if there are major players in Silicon Valley who are secretly invested in the Bill Simmons Media Group (again, we don’t know if they are nor who they are), and there is no way for readers to evaluate coverage or, as importantly, omissions on the industry.

All that being said, what Simmons is trying to do with The Ringer is a fascinating experiment. Yes, he’s trying to deeply enrich and indulge himself, but he’s also used his sway to employ 50 mostly-young men and women to pursue creativity. Everybody in media should be rooting for it to work in the long run.

[Ringer staff graphic by Michael Shamburger]